Stacey Dash's first major film role was in the Richard Pryor comedy Moving in 1988. Stacey Dash also had sizeable roles in Mo' Money and Renaissance Man during this time. In 1995, Stacey Dash starred as a femme fatale in a low budget film, Illegal in Blue. Stacey Dash received her big break with the 1995 film Clueless, which starred Alicia Silverstone and Brittany Murphy. Stacey Dash played Cher's high school best friend Dionne Marie Davenport, even though Dash was twenty-eight at the time. In 1996 the film spawned a television spinoff, also called Clueless, in which Stacey Dash reprised her role as Dionne and in which Rachel Blanchard played Cher. The series ran from 1996-1999.

A series of hit singles from her next studio albums, Like a Virgin (1984) and True Blue (1986), established her as a pop icon. Madonna pushed the boundaries of lyrical content in mainstream popular music and imagery in her music videos, which became a fixture on MTV. Her recognition was further raised by the film Desperately Seeking Susan (1985) which was widely seen as a Madonna vehicle, despite her not playing the lead. Expanding on the use of religious imagery with Like a Prayer (1989), Madonna was praised by critics for her diverse musical productions, while at the same time religious conservatives and the Vatican criticized her. In 1992, Madonna founded the Maverick corporation as a joint venture with Time Warner. The same year, Madonna expanded the use of sexually explicit material in her work, beginning with the release of the studio album Erotica, followed by the publishing of the coffee table book XXX, and release of the erotic thriller Body of Evidence, all of which received negative responses from conservatives and liberals alike.

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